3-[[(3aS,7aS)-2-Hydroxy-4-(benzyloxycarbonyl)octahydrofuro[3,2-b]pyridine-2-yl]methyl]-3,4-dihydroquinazoline-4-one

Base Information

• Chemical Name: 3-[[(3aS,7aS)-2-Hydroxy-4-(benzyloxycarbonyl)octahydrofuro[3,2-b]pyridine-2-yl]methyl]-3,4-dihydroquinazoline-4-one
• CAS No.: 304436-20-2
• Molecular Formula: C₂₄H₂₅N₃O₅
• Molecular Weight: 435.48
• DSSTox Substance ID: DTXSID601106126
• Nikkaji Number: J1.129.454E
• Mol file: 304436-20-2.mol

Synonyms:DTXSID601106126;3-[[(3aS,7aS)-2-Hydroxy-4-(benzyloxycarbonyl)octahydrofuro[3,2-b]pyridine-2-yl]methyl]-3,4-dihydroquinazoline-4-one;304436-20-2;Phenylmethyl (3aS,7aS)-hexahydro-2-hydroxy-2-[(4-oxo-3(4H)-quinazolinyl)methyl]furo[3,2-b]pyridine-4(2H)-carboxylate

Chemical Property of 3-[[(3aS,7aS)-2-Hydroxy-4-(benzyloxycarbonyl)octahydrofuro[3,2-b]pyridine-2-yl]methyl]-3,4-dihydroquinazoline-4-one

Chemical Property:

• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 435.17942091
• Heavy Atom Count: 32
• Complexity: 739

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC2C(CC(O2)(CN3C=NC4=CC=CC=C4C3=O)O)N(C1)C(=O)OCC5=CC=CC=C5
• Isomeric SMILES: C1C[C@H]2[C@H](CC(O2)(CN3C=NC4=CC=CC=C4C3=O)O)N(C1)C(=O)OCC5=CC=CC=C5

Technology Process of 3-[[(3aS,7aS)-2-Hydroxy-4-(benzyloxycarbonyl)octahydrofuro[3,2-b]pyridine-2-yl]methyl]-3,4-dihydroquinazoline-4-one

There total 8 articles about 3-[[(3aS,7aS)-2-Hydroxy-4-(benzyloxycarbonyl)octahydrofuro[3,2-b]pyridine-2-yl]methyl]-3,4-dihydroquinazoline-4-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

4-Hydroxyquinazoline (491-36-1) + (3aS,7aS)-2-Bromomethyl-2-hydroxy-hexahydro-furo[3,2-b]pyridine-4-carboxylic acid benzyl ester → benzyl (3aS,7aS)-2-hydroxy-2-[(4-oxo-3(4H)-quinazolinyl)methyl]hexahydrofuro[3,2-b]pyridine-4(2H)-carboxylate (304436-20-2)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 2h;

DOI:10.1039/b005028h

Reference yield:

Benzyl 2-allyl-3-oxo-1-piperidinecarboxylate (244056-97-1) → benzyl (3aS,7aS)-2-hydroxy-2-[(4-oxo-3(4H)-quinazolinyl)methyl]hexahydrofuro[3,2-b]pyridine-4(2H)-carboxylate (304436-20-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 62 percent / baker's yeast; sucrose; K₂CO₃ / H₂O; ethanol / 90 h / 15 °C

2: 87 percent / NBS / acetonitrile / 0.5 h / 20 °C

3: potassium tert-butoxide / tetrahydrofuran / 0.25 h / 20 °C

4: 2.17 g / NBS / tetrahydrofuran / 1 h / 20 °C

5: aq. HCl / acetonitrile / 1 h / 20 °C

6: 1.58 g / K₂CO₃ / dimethylformamide / 1 h / 20 °C

With hydrogenchloride; N-Bromosuccinimide; baker's yeast; potassium tert-butylate; potassium carbonate; Sucrose; In tetrahydrofuran; ethanol; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0040-4020(00)01109-1

Reference yield:

benzyl (2S,3S)-2-allyl-3-hydroxypiperidine-1-carboxylate (304436-17-7,244056-94-8) → benzyl (3aS,7aS)-2-hydroxy-2-[(4-oxo-3(4H)-quinazolinyl)methyl]hexahydrofuro[3,2-b]pyridine-4(2H)-carboxylate (304436-20-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 87 percent / NBS / acetonitrile / 0.5 h / 20 °C

2: potassium tert-butoxide / tetrahydrofuran / 0.25 h / 20 °C

3: 2.17 g / NBS / tetrahydrofuran / 1 h / 20 °C

4: aq. HCl / acetonitrile / 1 h / 20 °C

5: 1.58 g / K₂CO₃ / dimethylformamide / 1 h / 20 °C

With hydrogenchloride; N-Bromosuccinimide; potassium tert-butylate; potassium carbonate; In tetrahydrofuran; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0040-4020(00)01109-1

upstream raw materials:

4-Hydroxyquinazoline

Benzyl 2-allyl-3-oxo-1-piperidinecarboxylate

benzyl (R)-2-allyl-3-oxopiperidine-1-carboxylate

benzyl (2S,3S)-2-allyl-3-hydroxypiperidine-1-carboxylate

Downstream raw materials:

(+)-isofebrifugine

febrifugine